Single Family Homes For Sale in Chestertown, MD

42 homes

Use arrow keys to navigate
0.27 ACRES
$615,000
4 Beds
2.5 Baths
4,536 sqft
103 Maple Ave,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
Use arrow keys to navigate
NEW
COMING SOON 7/17
0.46 ACRES
$735,000
4 Beds
2.5 Baths
2,730 sqft
210 N Queen St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
Use arrow keys to navigate
NEW
COMING SOON 7/2
0.34 ACRES
$325,000
3 Beds
1 Bath
1,000 sqft
896 Washington Ave,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
Use arrow keys to navigate
2 ACRES
$279,900
3 Beds
2 Baths
1,296 sqft
22481 Goose Hollow Dr,
Chestertown, MD 21620
Keller Williams Legacy
Use arrow keys to navigate
OPEN SAT, 11-1PM
3D VIEW
0.76 ACRES
$468,000
3 Beds
2 Baths
3,262 sqft
25750 Collins Ave,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
Use arrow keys to navigate
0.34 ACRES
$324,900
3 Beds
1 Bath
1,248 sqft
517 Round Top Rd,
Chestertown, MD 21620
Keller Williams Flagship
Use arrow keys to navigate
3D VIEW
$515,000
2 Beds
2.5 Baths
1,476 sqft
101 S Mill St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
OPEN SAT, 11-1PM
0.61 ACRES
$1,200,000
4 Beds
3 Baths
2,292 sqft
202 Royston Shores Rd,
Chestertown, MD 21620
Cross Street Realtors LLC
$100,000
2 Beds
1 Bath
1,296 sqft
234 N College Ave,
Chestertown, MD 21620
Cummings & Co. Realtors
3D VIEW
9.2 ACRES
$1,650,000
9 Beds
6.5 Baths
4,776 sqft
8796 Maryland Pkwy,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$99,900
3 Beds
1.5 Baths
2,210 sqft
110 Prospect St,
Chestertown, MD 21620
ANR Realty, LLC
0.39 ACRES
$429,900
4 Beds
2.5 Baths
2,160 sqft
10781 Fermoy Rd,
Chestertown, MD 21620
Real Broker, LLC
3D VIEW
0.34 ACRES
$380,000
4 Beds
2 Baths
1,277 sqft
213 Byford Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.28 ACRES
$200,000
4 Beds
1 Bath
2,920 sqft
21172 Wyoming Ave,
Chestertown, MD 21620
Blue Star Real Estate, LLC
3.55 ACRES
$1,450,000
4 Beds
5 Baths
4,257 sqft
22470 Fairgale Farm Ln,
Chestertown, MD 21620
Gunther-McClary Real Estate
$425,000
2 Beds
3 Baths
1,518 sqft
522 High St,
Chestertown, MD 21620
Benson & Mangold, LLC
$329,900
3 Beds
2.5 Baths
1,896 sqft
102 Flying Cloud Dr,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
3D VIEW
0.51 ACRES
$389,000
3 Beds
2 Baths
1,120 sqft
240 Merganser Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
$385,000
5 Beds
3.5 Baths
2,534 sqft
107 Flying Cloud Dr,
Chestertown, MD 21620
CENTURY 21 New Millennium
0.41 ACRES
$309,900
4 Beds
2 Baths
1,325 sqft
304 Hadaway Dr,
Chestertown, MD 21620
Redfin Corporation
$340,000
4 Beds
2.5 Baths
1,972 sqft
214 Silver Heel Rd,
Chestertown, MD 21620
Cross Street Realtors LLC
$399,900
3 Beds
2.5 Baths
1,944 sqft
103 Trafford Dr,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
0.33 ACRES
$320,000
3 Beds
2 Baths
1,232 sqft
8706 Elm Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.55 ACRES
$299,000
3 Beds
1 Bath
1,120 sqft
208 Central Dr,
Chestertown, MD 21620
Redfin Corp
0.37 ACRES
$244,500
2 Beds
1 Bath
912 sqft
21217 Texas Ave,
Chestertown, MD 21620
RE/MAX Leading Edge
3D VIEW
$550,000
5 Beds
3.5 Baths
3,816 sqft
103 Sutton Way,
Chestertown, MD 21620
TTR Sotheby's International Realty
$865,000
3 Beds
3.5 Baths
2,472 sqft
106 S Queen St,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
1.1 ACRES
$524,900
3 Beds
2.5 Baths
2,268 sqft
101 Coleman Dr,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$198,000
3 Beds
1 Bath
1,200 sqft
139 Prospect St,
Chestertown, MD 21620
Redfin Corp
19.81 ACRES
$1,395,000
4 Beds
3.5 Baths
3,383 sqft
8276 Broad Neck Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
3D VIEW
0.76 ACRES
$344,900
3 Beds
2 Baths
1,392 sqft
109 Wilton Rd,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
3D VIEW
0.87 ACRES
$565,000
3 Beds
2.5 Baths
2,927 sqft
204 Double Creek Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.68 ACRES
$384,000
5 Beds
2.5 Baths
3,371 sqft
6746 Quaker Neck Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.28 ACRES
$450,000
4 Beds
2.5 Baths
2,880 sqft
110 Trafford Dr,
Chestertown, MD 21620
RE/MAX Advantage Realty
3D VIEW
$499,999
5 Beds
3.5 Baths
3,932 sqft
218 Camelot Dr,
Chestertown, MD 21620
Coldwell Banker Realty
$275,000
2 Beds
1.5 Baths
920 sqft
611 Cannon St,
Chestertown, MD 21620
Select Land & Homes, LLC
3D VIEW
$1,245,500
5 Beds
4.5 Baths
3,243 sqft
105 High St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$429,999
4 Beds
2 Baths
1,656 sqft
222 Mount Vernon Ave,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
3D VIEW
1.37 ACRES
$499,900
4 Beds
2.5 Baths
2,524 sqft
8620 Park Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
NEW - 2 DAYS AGO
0.67 ACRES
$320,000
3 Beds
1.5 Baths
1,096 sqft
222 Dutchess Rd,
Chestertown, MD 21620
Gunther-McClary Real Estate
Save Search in Chestertown, MD
Chestertown
House
Get emails when new homes match this search

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Single Family Homes For Sale in Chestertown, MD

42 homes

Save Search in Chestertown, MD

Nearby Real Estate

Nearby Zip Codes

Popular Cities in Maryland

Chestertown Neighborhoods

Chestertown Property Types

Real Estate Guides

Find Rental Properties